7-methoxy-4H-2,3-dioxo-1,4-benzoxazine | 81066-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-methoxy-4H-2,3-dioxo-1,4-benzoxazine
• 英文别名: 7-methoxy-4H-1,4-benzoxazine-2,3-dione
• CAS: 81066-48-0
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: QOVKOXBSXVSRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-4H-2,3-dioxo-1,4-benzoxazine 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以72%的产率得到2-羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮
  参考文献：
  名称：

  A New General Approach to the 2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one Skeleton via Diisobutylaluminum Hydride Reduction of 2,3-Dioxo-1,4-benzoxazines

  摘要：

  一系列天然半肟2a-d是通过化学选择性二异丁基氢化铝还原2,3-二氧代-4H-1,4-苯并恶嗪1a,b及其N-羟基衍生物1c,d前体合成的。所描述的工艺是一种新的通用方法，从2-羟基-2H-1,4-苯并恶嗪-3(4H)-酮骨架出发，仅通过三个步骤，从硝基苯酚开始，即可生成生物活性天然羟肟酸2,4-二羟基-2H-1,3(4H)-酮（2c）和2,4-二羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮（2d）。

  DOI：

  10.1055/s-1993-25936
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯酚钾 在 Pt(S)/C 甲醇 、 氢气 作用下， 以 甲苯 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 7-methoxy-4H-2,3-dioxo-1,4-benzoxazine
  参考文献：
  名称：

  Syntheses of Cyclic Hydroxamic Acids and Lactams with 2,3-dioxo-1,4-benzoxazine skeleton

  摘要：

  Ethyl 2-nitrophenyl oxalate (1 a) and its 5-methoxy derivative (1 b) were subjected to catalytic hydrogenations over 3 % Pt (S) on carbon in different solvents. Thus, hydrogenation in acetic acid yielded 4-hydroxy-2,3-dioxo-1,4-benzoxazine (2a) and its 7-methoxy derivative (2 b) by reductive cyclization, the dehydro forms of the naturally occurring cyclic hydroxamic acids DIBOA and DIMBOA from Gramineae. In contrast, hydrogenation of esters 1 in methanol results in the formation of amides 3 by acyl group migration. On heating, amides 3 undergo lactonization to form lactone-lactames 4, which in turn undergo ring opening to give amides 3 when refluxed in ethanol.

  DOI：

  10.1002/prac.19933350409

文献信息

• [1,4]Benzoxazine-2,3-diones as antiallergic agents
  作者：Bernard Loev、Howard Jones、Richard E. Brown、Fu Chih Huang、Atul Khandwala、Mitchell J. Leibowitz、Paula Sonnino-Goldman

  DOI：10.1021/jm00379a006

  日期：1985.1

  The synthesis of a series of [1,4]benzoxazine-2,3-diones and a new class of compounds, benzobisoxazinetetrones, is described. These compounds were evaluated for their effect in the rat mast cell (RMC) test passively sensitized in vitro with rat antiovalbumin serum and for their effect in inhibitory passive cutaneous anaphylaxis (PCA) in the rat. Some of these compounds are of the same potency level as disodium cromglycate in the RMC test and some are effective orally in PCA.
• LOEV, B.;JONES, H.;BROWN, R. E.;HUANG, FU-CHIH;KHANDWALA, A.;LEIBOWITZ, M+, J. MED. CHEM., 1985, 28, N 1, 24-27
  作者：LOEV, B.、JONES, H.、BROWN, R. E.、HUANG, FU-CHIH、KHANDWALA, A.、LEIBOWITZ, M+

  DOI：——

  日期：——
• Syntheses of Cyclic Hydroxamic Acids and Lactams with 2,3-dioxo-1,4-benzoxazine skeleton
  作者：H. Hartenstein、D. Sicker

  DOI：10.1002/prac.19933350409

  日期：——

  Ethyl 2-nitrophenyl oxalate (1 a) and its 5-methoxy derivative (1 b) were subjected to catalytic hydrogenations over 3 % Pt (S) on carbon in different solvents. Thus, hydrogenation in acetic acid yielded 4-hydroxy-2,3-dioxo-1,4-benzoxazine (2a) and its 7-methoxy derivative (2 b) by reductive cyclization, the dehydro forms of the naturally occurring cyclic hydroxamic acids DIBOA and DIMBOA from Gramineae. In contrast, hydrogenation of esters 1 in methanol results in the formation of amides 3 by acyl group migration. On heating, amides 3 undergo lactonization to form lactone-lactames 4, which in turn undergo ring opening to give amides 3 when refluxed in ethanol.
• A New General Approach to the 2-Hydroxy-2<i>H</i>-1,4-benzoxazin-3(4<i>H</i>)-one Skeleton via Diisobutylaluminum Hydride Reduction of 2,3-Dioxo-1,4-benzoxazines
  作者：Dieter Sicker、Holger Hartenstein

  DOI：10.1055/s-1993-25936

  日期：——

  A series of naturally occurring hemiacetals 2a-d was synthesized by the chemoselective diisobutylaluminum hydride reduction of 2,3-dioxo-4H-1, 4-benzoxazines 1a,b and their N-hydroxy derivatives 1c,d precursors. The procedure described represents a new general approach to the 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton giving rise to the bioactive natural hydroxamic acids 2,4-dihydroxy-2H-1, 3(4H)-one (2c) and 2,4-dihydroxy-7-methoxy-2H-1, 4-benzoxazin-3(4H)-one (2d) in only three steps starting from nitrophenols.

  一系列天然半肟2a-d是通过化学选择性二异丁基氢化铝还原2,3-二氧代-4H-1,4-苯并恶嗪1a,b及其N-羟基衍生物1c,d前体合成的。所描述的工艺是一种新的通用方法，从2-羟基-2H-1,4-苯并恶嗪-3(4H)-酮骨架出发，仅通过三个步骤，从硝基苯酚开始，即可生成生物活性天然羟肟酸2,4-二羟基-2H-1,3(4H)-酮（2c）和2,4-二羟基-7-甲氧基-2H-1,4-苯并恶嗪-3(4H)-酮（2d）。